WO2021010656A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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WO2021010656A1
WO2021010656A1 PCT/KR2020/009012 KR2020009012W WO2021010656A1 WO 2021010656 A1 WO2021010656 A1 WO 2021010656A1 KR 2020009012 W KR2020009012 W KR 2020009012W WO 2021010656 A1 WO2021010656 A1 WO 2021010656A1
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차용범
금수정
홍성길
김진주
이성재
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주식회사 엘지화학
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    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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Definitions

  • the present specification relates to an organic light emitting device.
  • the organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes.
  • a voltage is applied to the organic light emitting device having such a structure, electrons and electrons injected from the two electrodes are combined in the organic thin film to form a pair and then emit light while disappearing.
  • the organic thin film may be composed of a single layer or multiple layers as necessary.
  • Materials used in organic light-emitting devices are pure organic materials or complex compounds in which organic materials and metals form a complex, and depending on the use, hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. It can be classified as Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state upon oxidation is mainly used. Meanwhile, as an electron injection material or an electron transport material, an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state upon reduction is mainly used.
  • the light-emitting layer material a material having both p-type and n-type properties, that is, a material that is stable in both oxidation and reduction states, is preferable, and excitons generated by recombination of holes and electrons in the emission layer are formed.
  • a material having high luminous efficiency that converts it to light when it is formed is preferable.
  • Patent document 1 Korean Patent Publication No. 10-2017-058618
  • the organic light-emitting device comprising a first organic material layer provided between the first electrode and the emission layer
  • the first organic material layer includes a compound represented by Formula 1 below,
  • the light-emitting layer provides an organic light-emitting device comprising a compound represented by Formula 2 below.
  • Ar1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted divalent heterocyclic group,
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • r1 to r4 are the same as or different from each other, and each independently an integer of 0 to 4,
  • R7 to R11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • r7 is an integer from 1 to 3
  • r8 and r9 are the same as or different from each other, and each independently an integer of 1 to 5,
  • r10 and r11 are the same as or different from each other, and each independently an integer of 1 to 4,
  • the organic light-emitting device of the present invention includes the compound represented by Formula 1 in the first organic material layer and the compound represented by Formula 2 in the light-emitting layer, thereby obtaining an organic light-emitting device having a low driving voltage, high efficiency and/or long life. I can.
  • FIG. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 6, and a cathode 10.
  • FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, an electron transport layer 8, and a cathode 10 I did it.
  • FIG. 3 is a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a hole blocking layer (7), an electron transport layer (8).
  • An example of an organic light-emitting device comprising an electron injection layer 9 and a cathode 10 is shown.
  • the organic light emitting device of the present invention is a liquid crystal display.
  • the organic light-emitting device comprising a first organic material layer provided between the first electrode and the emission layer
  • the first organic material layer includes a compound represented by Formula 1 below,
  • the emission layer includes a compound represented by Formula 2 below.
  • Ar1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted divalent heterocyclic group,
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • r1 to r4 are the same as or different from each other, and each independently an integer of 0 to 4,
  • R7 to R11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • r7 is an integer from 1 to 3
  • r8 and r9 are the same as or different from each other, and each independently an integer of 1 to 5,
  • r10 and r11 are the same as or different from each other, and each independently an integer of 1 to 4,
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Silyl group; Boron group; Alkoxy group; Aryloxy group; Alkyl group; Cycloalkyl group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents.
  • a substituent to which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent to which two phenyl groups are connected.
  • substituted or unsubstituted refers to deuterium; Halogen group; Amine group; Silyl group; Alkyl group; Cycloalkyl group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents.
  • examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).
  • the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • oxygen of the ester group may be substituted with a C 1 to C 20 linear, branched or cyclic chain alkyl group or a C 6 to C 30 aryl group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the silyl group may be represented by the formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc., but is not limited thereto. Does not.
  • the boron group may be represented by the formula of -BY d Y e , wherein Y d and Y e are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the boron group includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.
  • the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms.
  • alkyl group examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, and the like, but are not limited thereto.
  • the alkoxy group may be linear, branched or cyclic.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 20 carbon atoms.
  • Substituents including an alkyl group, an alkoxy group and other alkyl group moieties described in the present specification include all of the straight chain or branched form.
  • the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are not limited thereto.
  • the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, and the like, but is limited thereto. no.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • Spirofluorenyl groups such as, (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.
  • aryl group in the aryloxy group may be described above with respect to the aryl group.
  • the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si, and Se as a hetero atom, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30.
  • heterocyclic group examples include a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group , Carbazole group, benzocarbazole group, naphthobenzofuran group, benzonaphthothiophene group, indenocarbazole group, and the like, but are not limited thereto.
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • ring in a substituted or unsubstituted ring formed by bonding with adjacent groups to each other, "ring" is a hydrocarbon ring; Or a hetero ring.
  • the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or an aryl group.
  • the description of the aryl group may be applied to the aromatic hydrocarbon ring.
  • the description of the aryl group may be applied except that the arylene group is divalent.
  • heteroaryl group In the present specification, the description of the heteroaryl group may be applied except that the heteroarylene group is divalent.
  • heterocyclic group In the present specification, the description of the heterocyclic group may be applied except that the divalent heterocycle is divalent.
  • Ar1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted divalent heterocyclic group,
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • r1 to r4 are the same as or different from each other, and each independently an integer of 0 to 4,
  • Ar1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • Ar1 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • Ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.
  • Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.
  • Ar1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heterocyclic group.
  • Ar1 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted C 2 to C 15 heterocyclic group.
  • Ar1 is a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Or a substituted or unsubstituted C 2 to C 10 heterocyclic group.
  • Ar1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted spirobifluorenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
  • Ar1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted spirobifluorenyl group.
  • Ar1 is a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, and an aryl group; A naphthyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group and an aryl group; A biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group and an aryl group; A terphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group and an aryl group; A phenanthrenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group and an aryl group; A triphenylenyl group un
  • Ar1 is a phenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with deuterium; Terphenyl group unsubstituted or substituted with deuterium; A phenanthrenyl group unsubstituted or substituted with deuterium; Triphenylenyl group unsubstituted or substituted with deuterium; A fluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, methyl group and phenyl group; Or a spirobifluorenyl group unsubstituted or substituted with deuterium.
  • Ar1 is a phenyl group unsubstituted or substituted with deuterium; Naphthyl group; A biphenyl group unsubstituted or substituted with deuterium; Terphenyl group; Phenanthrenyl group; Triphenylenyl group; Dimethylfluorenyl group; Diphenylfluorenyl group; Or a spirobifluorenyl group.
  • Ar1 is represented by any one of the following formulas.
  • R is hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • the dotted line indicates the binding position to be bonded to L1.
  • R is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • R is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R is an alkyl group having 1 to 30 carbon atoms; Or an aryl group having 6 to 30 carbon atoms.
  • R is a methyl group; Or a phenyl group.
  • Ar1 is represented by any one of the following formulas.
  • Ar1 is a phenyl group; Or a biphenyl group.
  • Ar1 may be substituted with deuterium.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted divalent heterocyclic group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 divalent heterocyclic group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 divalent heterocyclic group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 15 carbon atoms; Or a substituted or unsubstituted C 2 to C 15 divalent heterocyclic group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 10 carbon atoms; Or a substituted or unsubstituted C 2 to C 10 divalent heterocyclic group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted C 6 to C 30 arylene group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted C6 to C20 arylene group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylenylene group; Or a substituted or unsubstituted fluorenylene group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond;
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A phenylene group unsubstituted or substituted with deuterium, an alkyl group or an aryl group; A naphthylene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; A biphenylene group unsubstituted or substituted with deuterium, an alkyl group or an aryl group; Or a fluorenylene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; A phenylene group unsubstituted or substituted with deuterium; Naphthylene group; Biphenylene group; Or a dimethylfluorenylene group.
  • L1 is the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylenylene group; Or a substituted or unsubstituted fluorenylene group.
  • L1 is the same as or different from each other, and each independently a direct bond;
  • L1 is the same as or different from each other, and each independently a direct bond; A phenylene group unsubstituted or substituted with deuterium, an alkyl group or an aryl group; A naphthylene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; A biphenylene group unsubstituted or substituted with deuterium, an alkyl group or an aryl group; Or a fluorenylene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group.
  • L1 is the same as or different from each other, and each independently a direct bond; A phenylene group unsubstituted or substituted with deuterium; Naphthylene group; Biphenylene group; It is a dimethylfluorenylene group.
  • L2 is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
  • L2 is a phenylene group unsubstituted or substituted with deuterium or an aryl group; Or a biphenylene group unsubstituted or substituted with deuterium or an aryl group.
  • L3 is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
  • L3 is a phenylene group unsubstituted or substituted with deuterium or an aryl group; Or a biphenylene group unsubstituted or substituted with deuterium or an aryl group.
  • L2 and L3 are the same as or different from each other, and each independently a direct bond; A phenylene group unsubstituted or substituted with deuterium; Or a biphenylene group unsubstituted or substituted with deuterium.
  • L2 and L3 are the same as or different from each other, and each independently a direct bond; A phenylene group unsubstituted or substituted with deuterium; Or a biphenylene group.
  • L1 to L3 are direct bonds or are represented by any one of the following formulas.
  • R'and R'' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • the dotted line indicates the bonding position.
  • R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • R'and R'' are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R'and R'' are the same as or different from each other, and each independently an alkyl group having 1 to 30 carbon atoms; Or an aryl group having 6 to 30 carbon atoms.
  • R'and R'' are the same as or different from each other, and each independently a methyl group; Or a phenyl group.
  • L1 to L3 are direct bonds or are represented by any one of the following formulas.
  • the dotted line represents the bonding position
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a biphenylene group.
  • L1 to L3 are the same as or different from each other, and each independently a phenylene group; Or a biphenylene group.
  • L1 to L3 may each be substituted with deuterium.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted phenyl group.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a phenyl group.
  • R1 to R4 are hydrogen.
  • R5 and R6 are the same as or different from each other, and each independently hydrogen; Or a phenyl group.
  • R1 to R6 are hydrogen.
  • r1 to r4 are the same as or different from each other, and each independently an integer of 0 to 4, and when r1 to r4 is an integer of 2 or more, the substituents in parentheses are the same or different from each other.
  • r1 to r4 are integers of 1 to 4, respectively.
  • r1 to r4 are 1.
  • r1 to r4 are 4.
  • the compound represented by Formula 1 has a left-right symmetric structure with respect to the Z1 axis as shown in the following structural formula.
  • the compound represented by Formula 1 has a left and right asymmetric structure based on the Z1 axis as shown in the following structural formula.
  • R7 to R11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • r7 is an integer from 1 to 3
  • r8 and r9 are the same as or different from each other, and each independently an integer of 1 to 5,
  • r10 and r11 are the same as or different from each other, and each independently an integer of 1 to 4,
  • R7 to R11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R7 to R11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.
  • R7 to R11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heterocyclic group.
  • R7 to R11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted carbazole group; Or a substituted or unsubstituted hexahydrocarbazole group.
  • R7 is hydrogen; heavy hydrogen; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R7 is hydrogen; heavy hydrogen; An amine group unsubstituted or substituted by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; A silyl group unsubstituted or substituted by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; An alkyl group unsubstituted or substituted by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; An aryl group unsubstituted or substituted by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group,
  • R7 is hydrogen; heavy hydrogen; An amine group unsubstituted or substituted by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; A silyl group unsubstituted or substituted by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; An alkyl group unsubstituted or substituted by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; An aryl group unsubstituted or substituted by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group,
  • R7 is hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms; An amine group substituted or unsubstituted by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, a halogen group, a cycloalkyl group having 3 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; An aryl group having 6 to 20 carbon atoms substituted or unsubstituted by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and a silyl group; Or a heterocyclic group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.
  • R7 is hydrogen; heavy hydrogen; Methyl group; t-butyl group; Trimethylsilyl group; An amine group unsubstituted or substituted with one or more substituents selected from the group consisting of methyl group, t-butyl group, fluorine group, cyclohexyl group and phenyl group; A phenyl group unsubstituted or substituted with a trimethylsilyl group; A carbazole group unsubstituted or substituted with a methyl group or a t-butyl group; Or a hexahydrocarbazole group unsubstituted or substituted with a methyl group.
  • R7 is hydrogen; Methyl group; t-butyl group; Trimethylsilyl group; An amine group unsubstituted or substituted with one or more substituents selected from the group consisting of methyl group, t-butyl group, fluorine group, cyclohexyl group and phenyl group; A phenyl group unsubstituted or substituted with a trimethylsilyl group; A carbazole group unsubstituted or substituted with a methyl group or a t-butyl group; Or a hexahydrocarbazole group unsubstituted or substituted with a methyl group.
  • R7 is hydrogen; Methyl group; t-butyl group; Trimethylsilyl group; An amine group unsubstituted or substituted with a methyl group, a t-butyl group, or a phenyl group unsubstituted or substituted with a fluorine group; An amine group unsubstituted or substituted with a cyclohexyl group; A phenyl group unsubstituted or substituted with a trimethylsilyl group; a carbazole group unsubstituted or substituted with a t-butyl group; Or a hexahydrocarbazole group unsubstituted or substituted with a methyl group.
  • R7 is represented by any one of the following structural formulas.
  • R7 is represented by any one of the following structural formulas.
  • R7 is hydrogen; Or an amine group unsubstituted or substituted with a phenyl group unsubstituted or substituted with a t-butyl group.
  • R8 and R9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R8 and R9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.
  • R8 and R9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heterocyclic group.
  • R8 and R9 are the same as or different from each other, and each independently hydrogen;
  • An amine group unsubstituted or substituted by connecting one or more substituents or two or more substituents selected from the group consisting of deuterium, an alkyl group, a halogen group, a silyl group, a cycloalkyl group, and an aryl group;
  • R8 and R9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group in which one or more substituents selected from the group consisting of deuterium, an alkyl group, a halogen group, a silyl group, and an aryl group or two or more substituents are connected to each other; An amine group substituted or unsubstituted by connecting one or more substituents or two or more substituents selected from the group consisting of deuterium, an alkyl group, a halogen group, a silyl group and an aryl group; Deuterium, an alkyl group, a halogen group, a silyl group, and an aryl group unsubstituted or substituted by connecting one or more substituents or two or more substituents selected from the group consisting of aryl groups; Or a substituted or unsubstituted heterocyclic group by connecting
  • R8 and R9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms; An amine group substituted or unsubstituted by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms; Deuterium, an alkyl group having 1 to 10 carbon atoms, a halogen group and a silyl group, substituted or unsubstituted aryl group having 6 to 20 carbon atoms by connecting one or more substituents or two or more substituents; Or deuterium, one or more substituents selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms by linking with two or
  • R8 and R9 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; t-butyl group; An amine group unsubstituted or substituted with a phenyl group; A phenyl group substituted or unsubstituted by connecting one or more substituents or two or more substituents selected from the group consisting of deuterium, methyl group, t-butyl group, fluorine group and silyl group; Or one or more substituents selected from the group consisting of deuterium, methyl group, t-butyl group, or phenyl group, or a substituted or unsubstituted pyridyl group by connecting two or more substituents.
  • R8 and R9 are the same as or different from each other, and each independently hydrogen; Methyl group; t-butyl group; Diphenylamine group; A phenyl group unsubstituted or substituted with deuterium, methyl group, t-butyl group, fluorine group, CF 3 or trimethylsilyl group; Or a methyl group, t-butyl group, CD 3 or a phenyl group substituted or unsubstituted pyridyl group.
  • R8 and R9 are the same as or different from each other, and each independently may be represented by any one of the following structural formulas.
  • R8 and R9 are the same as or different from each other, and each independently may be represented by any one of the following structural formulas.
  • R8 and R9 are the same as or different from each other, and each independently hydrogen; Or t-butyl group.
  • R10 and R11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R10 and R11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An amine group unsubstituted or substituted with an alkyl group, an arylalkyl group, or an aryl group; An alkyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with an alkyl group or an aryl group; Or a heterocyclic group unsubstituted or substituted with an alkyl group or an aryl group.
  • R10 and R11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An amine group unsubstituted or substituted with an alkyl group or an aryl group; An alkyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with an alkyl group or an aryl group; Or a heterocyclic group unsubstituted or substituted with an alkyl group or an aryl group.
  • R10 and R11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; An amine group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an arylalkyl group having 6 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; An alkyl group having 1 to 10 carbon atoms; Aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 2 to 20 carbon atoms.
  • R10 and R11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; An amine group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms; An alkyl group having 1 to 10 carbon atoms; Aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 2 to 20 carbon atoms.
  • R10 and R11 are the same as or different from each other, and each independently hydrogen; Methyl group; t-butyl group; Trimethylsilyl group; Phenyl group; Carbazole; Or an amine group substituted with a phenyl group.
  • R10 and R11 are the same as or different from each other, and each independently hydrogen; Methyl group; t-butyl group; Trimethylsilyl group; Phenyl group; Carbazole; Or a diphenylamine group.
  • R10 and R11 are a substituted or unsubstituted carbazole group or a substituted or unsubstituted amine group, the other is hydrogen.
  • R10 and R11 are the same as or different from each other, and each independently may be represented by any one of the following structural formulas.
  • R10 and R11 are the same as or different from each other, and each independently may be represented by any one of the following structural formulas.
  • R10 and R11 are hydrogen; Or t-butyl group.
  • r7 is an integer of 1 to 3.
  • r7 is 1.
  • r8 and r9 are integers of 1 to 5.
  • r8 and r9 are integers of 1 to 3.
  • r10 and r11 are integers of 1 to 4.
  • r10 and r11 are 1.
  • r7 to r11 is an integer of 2 or more
  • the substituents in parentheses are the same or different from each other.
  • Chemical Formula 2 is represented by the following Chemical Formula 2-1 or 2-2.
  • R8 to R11 and r7 to r11 are the same as those in Formula 2,
  • R7' is hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • G1 and G2 are the same as or different from each other, and each independently a substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group, or combine with an adjacent group to form a ring.
  • R7' is hydrogen; heavy hydrogen; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • R7' is hydrogen; heavy hydrogen; A silyl group unsubstituted or substituted by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; An alkyl group unsubstituted or substituted by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; Or a substituted or unsubstituted aryl group by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group.
  • R7' is hydrogen; heavy hydrogen; A silyl group unsubstituted or substituted by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; An alkyl group unsubstituted or substituted by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; Or a substituted or unsubstituted aryl group by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group.
  • R7' is hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms by connecting one or more substituents or two or more substituents selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and a silyl group.
  • R7' is hydrogen; heavy hydrogen; Methyl group; t-butyl group; Trimethylsilyl group; Or a phenyl group unsubstituted or substituted with a trimethylsilyl group.
  • R7' is hydrogen; Methyl group; t-butyl group; Trimethylsilyl group; Or a phenyl group unsubstituted or substituted with a trimethylsilyl group.
  • R7' is hydrogen; Methyl group; t-butyl group; Trimethylsilyl group; Or a phenyl group unsubstituted or substituted with a trimethylsilyl group.
  • R7' is represented by any one of the following structural formulas.
  • G1 and G2 are the same as or different from each other, and each independently a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 2 to 30 carbon atoms, or combined with an adjacent group to form a ring having 2 to 30 carbon atoms.
  • G1 and G2 are the same as or different from each other, and each independently a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 2 to 20 carbon atoms, or combined with an adjacent group to form a ring having 2 to 20 carbon atoms.
  • G1 and G2 are the same as or different from each other, and each independently an alkyl group or a cycloalkyl group unsubstituted or substituted with a halogen group; Or an aryl group unsubstituted or substituted with an alkyl group or a halogen group, or a carbazole ring unsubstituted or substituted with an alkyl group or a halogen group by bonding with adjacent groups; Or, it forms a hexahydrocarbazole ring unsubstituted or substituted with an alkyl group or a halogen group.
  • G1 and G2 are the same as or different from each other, and each independently a cycloalkyl group having 3 to 20 carbon atoms; Or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or a fluorine group, or a carbazole ring unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms by bonding with adjacent groups; Alternatively, a hexahydrocarbazole ring substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms is formed.
  • G1 and G2 are the same as or different from each other, and each independently a cyclohexyl group; Or a methyl group, t-butyl group, or a phenyl group unsubstituted or substituted with a fluorine group, or a carbazole ring unsubstituted or substituted with a t-butyl group by bonding with an adjacent group; Or to form a hexahydrocarbazole ring unsubstituted or substituted with a methyl group.
  • -N(G1)(G2) is represented by any one of the following structural formulas.
  • -N(G1)(G2) is represented by any one of the following structural formulas.
  • Formula 2-1 is represented by the following Formula 2-1-1.
  • R7', R8 to R11, and r7 to r11 are the same as those in Formula 2-1.
  • R8 and R9 in Formula 2 are 1, R8 and R9 are bonded to the ortho position from the position where N and the phenyl group are connected.
  • r8 when r8 is 2 or more in Formula 2, at least one of the two or more R8 is bonded to the ortho position from the position where N and the phenyl group are connected.
  • r9 in Formula 2 when r9 in Formula 2 is 2 or more, at least one of the two or more R9 is bonded to the ortho position from the position where N and the phenyl group are connected.
  • the compound represented by Formula 2 has a left-right symmetric structure with respect to the Z2 axis as shown in the following structural formula.
  • the compound represented by Formula 2 has a left and right asymmetric structure based on the Z2 axis as shown in the following structural formula.
  • the compound represented by Formula 1 is represented by any one of the following structural formulas.
  • the compound represented by Formula 2 is represented by any one of the following structural formulas.
  • compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above.
  • the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure of the above structure.
  • the compounds of Formulas 1 and 2 of the present invention may have a core structure as shown in Formulas 1 and 2 below.
  • Substituents may be bonded by methods known in the art, and the type, position, and number of substituents may be changed according to techniques known in the art.
  • the organic light-emitting device of the present invention can be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except for forming the light-emitting layer using the compounds of Formulas 1 and 2 described above.
  • the compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • the organic light-emitting device of the present invention may include one or more organic material layers between the first electrode and the second electrode.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light-emitting device of the present invention includes one or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as an organic material layer. It can have a structure to However, the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic material layers.
  • the organic light-emitting device of the present invention includes an emission layer, the first organic material layer provided between the first electrode and the emission layer includes a compound represented by Formula 1, and the emission layer includes a compound represented by Formula 2.
  • the thickness of the first organic material layer including Formula 1 is 30 ⁇ to 300 ⁇ , preferably 50 ⁇ to 200 ⁇ .
  • the first organic material layer of the organic light emitting device of the present invention may be a hole transport layer or an electron blocking layer.
  • the first organic material layer of the organic light emitting device of the present invention includes an electron blocking layer, and the electron blocking layer includes a compound represented by Formula 1 above.
  • the first organic material layer of the organic light emitting device of the present invention is an electron blocking layer, and the electron blocking layer includes a compound represented by Formula 1 above.
  • the emission layer of the organic light-emitting device of the present invention includes a dopant, and the dopant is a compound represented by Formula 2 above.
  • the first organic material layer of the organic light emitting device of the present invention includes a compound represented by Formula 1 as a hole transport layer, and the emission layer includes a compound represented by Formula 2 as a dopant of the emission layer.
  • the first organic material layer of the organic light emitting device of the present invention includes a compound represented by Formula 1 as an electron blocking layer, and the emission layer includes a compound represented by Formula 2 as a dopant of the emission layer.
  • the first organic material layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Chemical Formula 1.
  • the emission layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Chemical Formula 2.
  • the content of the compound represented by Formula 2 is 0.01 parts by weight to 30 parts by weight; Preferably 0.1 to 20 parts by weight; More preferably, it is 0.5 parts by weight to 10 parts by weight.
  • An organic light-emitting device satisfying the weight part exhibits excellent characteristics in terms of driving voltage, luminous efficiency, or lifetime.
  • the emission layer further includes a compound represented by the following formula (H).
  • L21 to L23 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • m 0 or 1.
  • L21 to L23 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroarylene group.
  • L21 to L23 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylene group; Naphthylene group; Divalent dibenzofuran group; Or a divalent dibenzothiophene group.
  • Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.
  • Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group; Or a substituted or unsubstituted monocyclic to 4 ring heteroaryl group.
  • Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted phenalene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsub
  • Ar21 to Ar23 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A biphenyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A naphthyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A dibenzofuran group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A naphthobenzofuran group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A dibenzothiophene group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; Or a naphthobenzothiophene group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms
  • the compound represented by Formula H is any one selected from the following compounds.
  • the organic light emitting device includes an emission layer, the emission layer includes the compound represented by Formula 2 as a dopant of the emission layer, and the compound represented by Formula H as a host of the emission layer.
  • the content of the compound represented by Formula 2 is 0.01 parts by weight to 30 parts by weight; 0.1 parts by weight to 20 parts by weight; Or 0.5 parts by weight to 10 parts by weight.
  • the emission layer may further include one host material in addition to the compound represented by Formula H.
  • the host material (mixed host compound) further included may include a condensed aromatic ring derivative or a heterocyclic-containing compound.
  • condensed aromatic ring derivatives include pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds in addition to anthracene derivatives
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, triazine derivatives, and the like, and may be a mixture of two or more thereof, but are not limited thereto.
  • the weight ratio of the compound represented by Formula H and the mixed host compound is 95:5 to 5:95, more preferably 30:70 to 70:30.
  • the emission layer includes one or two or more compounds represented by Formula H.
  • the light emitting layer including the compound represented by Formula 2 and the compound represented by Formula H has a blue color.
  • the organic light-emitting device includes two or more light-emitting layers, and at least one of the two or more light-emitting layers includes a compound represented by Formula 2 and a compound represented by Formula H.
  • the light emitting layer including the compound represented by Formula 2 and the compound represented by Formula H is blue, and the light emitting layer not including the compound represented by Formula 2 and the compound represented by Formula H is blue, known in the art, It may include a red or green light emitting compound.
  • the organic light emitting device has a structure in which the first organic material layer and the light emitting layer are adjacent to each other.
  • the organic material layer may include a hole blocking layer, and a material known in the art may be used for the hole blocking layer.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the organic light-emitting device may have, for example, a stacked structure as described below, but is not limited thereto.
  • the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the structure of the organic light-emitting device of the present invention may have a structure as shown in FIGS. 1 to 3, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 6, and a cathode 10 are sequentially stacked on a substrate 1.
  • the compound may be included in the light emitting layer 6.
  • FIG. 2 shows an organic light-emitting device in which an anode 2, a hole injection layer 3, a hole transport layer 6, a light emitting layer 6, an electron transport layer 8, and a cathode 10 are sequentially stacked on a substrate 1.
  • the structure is illustrated.
  • the compound may be included in the hole injection layer 3, the hole transport layer 6, the light emitting layer 6, or the electron transport layer 8.
  • FIG. 3 shows an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a hole blocking layer (7), an electron transport layer (8) on the substrate (1).
  • An example of an organic light-emitting device comprising an electron injection layer 9 and a cathode 10 is shown.
  • the compound is the hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron transport layer (8) or electron injection It may be included in layer 9.
  • the organic light-emitting device uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and uses a metal or conductive metal oxide or alloy thereof on a substrate.
  • PVD physical vapor deposition
  • an anode formed by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • One or more organic material layers are provided between the first electrode and the second electrode, and the organic material layer includes a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, And it may further include one or more of the hole transport and injection layer.
  • the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting electrons, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron transport and injection layer, etc. It may not have a single layer structure.
  • the organic material layer is made of a variety of polymer materials, and is used in a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made in layers.
  • the anode is an electrode for injecting holes, and a material having a large work function is preferably used as the anode material to facilitate hole injection into an organic material layer.
  • the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode is an electrode for injecting electrons
  • the cathode material is usually a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer
  • the hole injection material is a material capable of receiving holes from the anode at a low voltage, and is a high occupied HOMO (highest occupied material) of the hole injection material. It is preferable that molecular orbital) is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • the thickness of the hole injection layer may be 1 to 150 nm.
  • the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing deterioration of the hole injection characteristics, and when the thickness of the hole injection layer is 150 nm or less, the thickness of the hole injection layer is too thick to increase the driving voltage to improve the movement of holes. There is an advantage that can prevent it.
  • the hole transport layer may serve to facilitate transport of holes.
  • the hole transport material a material capable of transporting holes from the anode or the hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • a hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the electron blocking layer the above-described compound or a material known in the art may be used.
  • the organic light emitting device may further include one or more emission layers in addition to the emission layer.
  • the emission layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material.
  • the light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compound
  • Benzoxazole, benzthiazole, and benzimidazole-based compounds include Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • Examples of the host material for the light emitting layer include condensed aromatic ring derivatives or heterocyclic compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the emission dopants include PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium). ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum), but is not limited thereto.
  • a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant.
  • a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum)
  • Alq3 tris(8-hydroxyquinolino)aluminum
  • the light emitting dopant is a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distillbenzene (DSB), distrylarylene (DSA),
  • a fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.
  • a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
  • the electron transport layer may serve to facilitate transport of electrons.
  • the electron transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the thickness of the electron transport layer may be 1 to 50 nm.
  • the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing deterioration of the electron transport characteristics, and if the thickness of the electron transport layer is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in the driving voltage to improve the movement of electrons. There is an advantage to be able to.
  • the electron injection layer may serve to facilitate injection of electrons.
  • the electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and , A compound having excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • the metal complex compound examples include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.
  • the hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but are not limited thereto.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • Compound 2-2 was synthesized in the same manner as the synthesis of Compound 2-1 in Preparation Example 4, except that Intermediate B was used instead of Intermediate A in Preparation Example 4.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000 ⁇ was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • a compound of the following compound HI-1 and the following compound HI-2 was thermally vacuum deposited to a thickness of 100 ⁇ in a ratio of 98:2 (molar ratio) to form a hole injection layer.
  • a hole transport layer was formed by vacuum deposition of a compound (1150 ⁇ ) represented by the following formula HT-1, which is a material for transporting holes, on the hole injection layer.
  • the following compound EB-1 was vacuum-deposited on the hole transport layer with a film thickness of 50 ⁇ to form an electron blocking layer.
  • a light emitting layer was formed by vacuum depositing a compound represented by the following formula BH-1 and a compound represented by the following formula BD-1 with a film thickness of 200 ⁇ on the electron blocking layer at a weight ratio of 25:1.
  • a hole blocking layer was formed by vacuum depositing the following compound HB-1 with a film thickness of 50 ⁇ on the emission layer.
  • the following compound ET-1 and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron transport layer having a thickness of 300 ⁇ .
  • Lithium fluoride (LiF) in a thickness of 12 ⁇ and aluminum in a thickness of 2,000 ⁇ were sequentially deposited on the electron transport layer to form an electron injection layer and a negative electrode, respectively.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride at the cathode was 0.3 ⁇ /sec
  • the deposition rate of aluminum was 2 ⁇ /sec
  • the vacuum degree during deposition was 2 ⁇ 10 ⁇ Maintaining 7 ⁇ 5 ⁇ 10 -6 torr, an organic light emitting device was manufactured.
  • the compound used in Comparative Example 1 is as follows.
  • Comparative Example 1 an organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds shown in Table 1 below were used instead of the electron blocking layer compound EB-1 and the dopant compound BD-1, respectively.
  • the compounds used in Examples and Comparative Examples are as follows.
  • T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.
  • the organic light-emitting device of the embodiment in which the compound represented by Formula 1 is used as an electron blocking layer material and the compound represented by Formula 2 is used as a dopant material for the emission layer at the same time includes Formulas 1 and 2 Compared to the organic light emitting diodes of Comparative Examples 2 to 13 and 16 to 21 employing one of the compounds represented by, it exhibited excellent characteristics in terms of driving voltage, luminous efficiency and lifetime.
  • the organic light-emitting device of the embodiment according to the present invention employing both the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 improves efficiency and lifetime characteristics at the same time.
  • the organic light-emitting device employing a combination of the compounds of the present invention has significantly improved device characteristics compared to the comparative example device. It can be seen that it represents.

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Abstract

La présente invention concerne un élément électroluminescent organique comprenant : une première électrode ; une seconde électrode ; une couche électroluminescente disposée entre la première électrode et la seconde électrode ; et une première couche de matériau organique disposée entre la première électrode et la couche électroluminescente, la première couche de matériau organique comprenant un composé représenté par la formule chimique 1, et la couche électroluminescente comprenant un composé représenté par la formule chimique 2.
PCT/KR2020/009012 2019-07-18 2020-07-09 Élément électroluminescent organique WO2021010656A1 (fr)

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EP4322730A3 (fr) * 2021-09-16 2024-02-21 Samsung Display Co., Ltd. Dispositif électroluminescent organique et composé polycyclique fusionné pour dispositif électroluminescent organique

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KR20240020458A (ko) * 2022-08-08 2024-02-15 주식회사 엘지화학 유기 발광 소자

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